Nineteen transsexuals, approved for sex reassignement, were followed-up after 5 years. Outcome was evaluated as changes in seven areas of social, psychological, and psychiatric functioning. At baseline the patients were evaluated according to axis I, II, V (DSM-III-R), SCID screen, SASB (Structural Analysis of Social Behavior), and DMT (Defense Mechanism Test). At follow-up all but 1 were treated with contrary sex hormones, 12 had completed sex reassignment surgery, and 3 females were waiting for phalloplasty. One male transsexual regretted the decision to change sex and had quit the process. Two transsexuals had still not had any surgery due to older age or ambivalence. Overall, 68% (n = 13) had improved in at least two areas of functioning. In 3 cases (16%) outcome were judged as unsatisfactory and one of those regarded sex change as a failure. Another 3 patients were mainly unchanged after 5 years. Female transsexuals had a slightly better outcome, especially concerning establishing and maintaining partnerships and improvement in socio-economic status compared to male transsexuals. Baseline factors associated with negative outcome (unchanged or worsened) were presence of a personality disorder and high number of fulfilled axis II criteria. SCID screen assessments had high prognostic power. Negative self-image, according to SASB, predicted a negative outcome, whereas DMT variables were not correlated to outcome.